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(Synonyms: 去甲托品醇; Nortropenol) 目录号 : GC39499

Nortropine Hydrochloride (Nortropeno) is a secondary metabolite of tropine derivative drugs, such as atropine and benztropine.

Nortropine Chemical Structure

Cas No.:538-09-0

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100mg
¥495.00
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产品描述

Nortropine Hydrochloride (Nortropeno) is a secondary metabolite of tropine derivative drugs, such as atropine and benztropine.

Chemical Properties

Cas No. 538-09-0 SDF
别名 去甲托品醇; Nortropenol
Canonical SMILES O[C@H]1C[C@H](N2)CC[C@H]2C1
分子式 C7H13NO 分子量 127.18
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 7.8629 mL 39.3144 mL 78.6287 mL
5 mM 1.5726 mL 7.8629 mL 15.7257 mL
10 mM 0.7863 mL 3.9314 mL 7.8629 mL
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Research Update

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Molecules 2021 Mar 23;26(6):1813.PMID:33807018DOI:10.3390/molecules26061813.

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (Nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

Atropine Metabolism by Pseudomonas sp. Strain AT3: Evidence for Nortropine as an Intermediate in Tropine Breakdown and Reactions Leading to Succinate

Appl Environ Microbiol 1996 Sep;62(9):3245-50.PMID:16535398DOI:10.1128/aem.62.9.3245-3250.1996.

Pseudomonas strain AT3, isolated by elective culture with atropine, hydrolyzed atropine and grew diauxically, first on the tropic acid and then on the tropine. Tropine was also used as a sole carbon and energy source. The methyl group of tropine was eliminated as formaldehyde, and the Nortropine thus formed was a precursor of 6-hydroxycyclohepta-1,4-dione. Ammonia was detected as a product of nitrogen elimination. 6-Hydroxycyclohepta-1,4-dione was oxidized to cyclohepta-1,3,5-trione by an induced NAD(sup+)-specific dehydrogenase. Although cyclohepta-1,3,5-trione is a (beta)-diketone with two potential hydrolytic cleavage sites, an induced hydrolase was specific for one of these sites, with 4,6-dioxoheptanoate as the only hydrolysis product. Unlike the alternative cleavage product (3,6-dioxoheptanoate), this compound is also a (beta)-diketone, and a second hydrolytic cleavage formed succinate and acetone. Although Pseudomonas strain AT3 was not capable of growth with acetone, the compound was not detected in the culture medium and may have been lost to the atmosphere. Exhaustive experimentation with a wide range of conditions did not result in detection of the enzymes required for cleavage of the carbon-nitrogen bonds leading to the formation of Nortropine and 6-hydroxycyclohepta-1,4-dione.

[Electrochemical Analysis Using Organic Nitroxyl Radicals]

Yakugaku Zasshi 2023;143(2):95-100.PMID:36724933DOI:10.1248/yakushi.22-00143.

Organic nitroxyl radicals represented by 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) are known to be compounds that catalyze alcohol oxidation reactions. These catalytic reactions can be applied to a wide range of compounds with hydroxy and amino groups. It is also possible to selectively oxidize primary alcohols by designing the skeleton around the nitroxyl radical moiety for use in organic synthesis. Reactions can also be carried out by electrochemical methods, and the electrical current measured during the reaction can be used to quantify the substrates. Therefore, the combination of reactions catalyzed by nitroxyl radicals and electrochemical techniques is expected to be applied as a new analytical method. However, since the reaction does not proceed rapidly in neutral aqueous solutions, it has mostly been applied in basic aqueous solutions or organic solvents, and there have been no reports on sensor applications under physiological conditions. Herein, we have developed a novel catalyst, Nortropine N-oxyl (NNO), which is highly active even in neutral aqueous solutions, and have found that it can be used for the analysis of biological components and drugs under physiological conditions. The combination of this method with enzymatic reactions made it possible to specifically detect certain compounds. In this review, we describe a novel analytical method that combines these nitroxyl radicals with electrochemical methods.

Tropine derivatives with central activities. Part II: Solvolysis of N-substituted Nortropine methanesulfonates

Arzneimittelforschung 1976;26(10):1797-800.PMID:191036doi

The preparation and the reaction kinetical properties in solvolysis of a series of N-substituted Nortropine methanesulfonates 1-8 are described. It was found that the rate of solvolysis depends on the nature of the N-substituents considerably. The solvolysis rates can be brought into correlation with the electron donating and withdrawing and steric properties of the N-substituents. Methane-sulfonates of other two bicyclic aminoalcohols 10, 11 were also prepared and kinetically studied.

Catalysis of electro-oxidation of antibiotics by nitroxyl radicals and the electrochemical sensing of vancomycin

RSC Adv 2021 Jun 18;11(35):21622-21628.PMID:35478798DOI:10.1039/d1ra03681e.

Quantifying drug concentrations in vivo quickly and easily is possible using electrochemical methods. The present study describes the electrochemical detection of vancomycin (VCM) and other antibiotics from the current obtained using nitroxyl radicals as electrocatalysts. Nortropine N-oxyl (NNO), which is more active than 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO), a typical nitroxyl radical compound, produced greater current values for drugs with intramolecular hydroxy groups and secondary and tertiary amines. However, because the catalytic action of NNO is inactivated by primary amines in the substrate, VCM and teicoplanin with primary amines could not be detected. TEMPO was less active than NNO but not inactivated against primary amines. Therefore, electrochemical sensing of vancomycin was done using 4-acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (A-TEMPO), which has a greater oxidation capacity than TEMPO due to its electron-withdrawing groups. As a result, the current of A-TEMPO increased in the low concentration range of VCM as compared to TEMPO. This method also was able to quantify VCM in the concentration range of 10-100 μM, which is an important concentration range for drug monitoring in blood.